# Electronic Supplementary Material (ESI) for Polymer Chemistry.
# This journal is © The Royal Society of Chemistry 2015

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_a10315c
_audit_block_doi                 10.5517/cc14j0b0
_database_code_depnum_ccdc_archive 'CCDC 1058071'
_audit_update_record             
;
2015-04-06 deposited with the CCDC.
2015-08-31 downloaded from the CCDC.
;

_refine_special_details          SQUEEZE
_platon_squeeze_details          
; 
The disordered solvent molecules cannot be modeled and were treated 
by SQUEEZE,PLATON.
There are total 439e per unit cell were accumulated which corresponds 
to 55e per formula(C24H12N6O6). The 55e might come from 
water molecules and were not included in the formula.
;



_audit_creation_method           SHELXL-97
_chemical_name_systematic        a10315c
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         C24H12N6O6
_chemical_formula_sum            'C24 H12 N6 O6'
_chemical_formula_weight         480.40

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Orthorhombic
_symmetry_space_group_name_H-M   Pbcn

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y+1/2, z+1/2'
'-x, y, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y-1/2, -z-1/2'
'x, -y, z-1/2'
'-x-1/2, y-1/2, z'

_cell_length_a                   7.235(2)
_cell_length_b                   41.244(13)
_cell_length_c                   21.816(7)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     6510(4)
_cell_formula_units_Z            8
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    741
_cell_measurement_theta_min      2.858
_cell_measurement_theta_max      18.707

_exptl_crystal_description       sheet
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.04
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    0.980
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1968
_exptl_absorpt_coefficient_mu    0.073
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9891
_exptl_absorpt_correction_T_max  0.9971
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            25344
_diffrn_reflns_av_R_equivalents  0.1388
_diffrn_reflns_av_sigmaI/netI    0.1906
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -48
_diffrn_reflns_limit_k_max       40
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         1.36
_diffrn_reflns_theta_max         25.00
_reflns_number_total             5744
_reflns_number_gt                1499
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SHELXTL'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'



_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0912P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         5744
_refine_ls_number_parameters     325
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1998
_refine_ls_R_factor_gt           0.0662
_refine_ls_wR_factor_ref         0.1945
_refine_ls_wR_factor_gt          0.1531
_refine_ls_goodness_of_fit_ref   0.665
_refine_ls_restrained_S_all      0.665
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.2308(7) -0.01265(13) 0.5120(3) 0.0879(17) Uani 1 1 d . . .
N2 N 0.6924(9) 0.14159(19) 0.3401(2) 0.106(2) Uani 1 1 d . . .
N3 N 0.6314(7) 0.35780(12) 0.5689(3) 0.0865(17) Uani 1 1 d . . .
N4 N 0.4749(4) 0.10329(8) 0.68604(17) 0.0468(10) Uani 1 1 d . . .
N5 N 0.5360(4) 0.16052(8) 0.62451(17) 0.0497(10) Uani 1 1 d . . .
N6 N 0.5256(5) 0.21917(8) 0.68825(15) 0.0459(9) Uani 1 1 d . . .
O1 O 0.2470(8) -0.03699(10) 0.5399(3) 0.163(3) Uani 1 1 d . . .
O2 O 0.1619(6) -0.00997(11) 0.4595(3) 0.1230(19) Uani 1 1 d . . .
O3 O 0.7819(9) 0.11960(13) 0.3164(2) 0.162(3) Uani 1 1 d . . .
O4 O 0.6341(7) 0.16440(15) 0.31196(19) 0.140(2) Uani 1 1 d . . .
O5 O 0.5902(6) 0.35532(10) 0.5138(2) 0.1119(17) Uani 1 1 d . . .
O6 O 0.6978(6) 0.38220(9) 0.5922(2) 0.1202(18) Uani 1 1 d . . .
C1 C 0.2979(7) 0.01815(12) 0.5425(3) 0.0623(15) Uani 1 1 d . . .
C2 C 0.4033(8) 0.01557(12) 0.5935(3) 0.0738(16) Uani 1 1 d . . .
H2A H 0.4323 -0.0045 0.6105 0.089 Uiso 1 1 calc R . .
C3 C 0.4659(6) 0.04434(12) 0.6190(2) 0.0643(14) Uani 1 1 d . . .
H3A H 0.5432 0.0435 0.6531 0.077 Uiso 1 1 calc R . .
C4 C 0.4177(6) 0.07374(11) 0.5959(2) 0.0485(12) Uani 1 1 d . . .
C5 C 0.3083(7) 0.07472(10) 0.5451(2) 0.0619(14) Uani 1 1 d . . .
H5A H 0.2746 0.0947 0.5290 0.074 Uiso 1 1 calc R . .
C6 C 0.2455(6) 0.04655(12) 0.5167(2) 0.0640(14) Uani 1 1 d . . .
H6A H 0.1715 0.0472 0.4818 0.077 Uiso 1 1 calc R . .
C7 C 0.4782(5) 0.10357(10) 0.6246(2) 0.0417(11) Uani 1 1 d . . .
C8 C 0.5271(6) 0.13267(10) 0.5938(2) 0.0440(12) Uani 1 1 d . . .
C9 C 0.5707(6) 0.13530(10) 0.5286(2) 0.0462(12) Uani 1 1 d . . .
C10 C 0.6630(7) 0.10985(11) 0.4993(2) 0.0608(14) Uani 1 1 d . . .
H10A H 0.6978 0.0917 0.5217 0.073 Uiso 1 1 calc R . .
C11 C 0.7029(7) 0.11142(12) 0.4375(3) 0.0731(16) Uani 1 1 d . . .
H11A H 0.7616 0.0943 0.4177 0.088 Uiso 1 1 calc R . .
C12 C 0.6538(7) 0.13885(14) 0.4063(2) 0.0632(15) Uani 1 1 d . . .
C13 C 0.5720(7) 0.16487(12) 0.4346(2) 0.0626(14) Uani 1 1 d . . .
H13A H 0.5448 0.1836 0.4125 0.075 Uiso 1 1 calc R . .
C14 C 0.5305(6) 0.16295(12) 0.4964(2) 0.0586(13) Uani 1 1 d . . .
H14A H 0.4753 0.1804 0.5162 0.070 Uiso 1 1 calc R . .
C15 C 0.5006(5) 0.13151(9) 0.71664(18) 0.0403(11) Uani 1 1 d . . .
C16 C 0.5136(5) 0.16044(10) 0.6863(2) 0.0452(12) Uani 1 1 d . . .
C17 C 0.5102(5) 0.19118(9) 0.71830(17) 0.0408(11) Uani 1 1 d . . .
C18 C 0.5188(6) 0.24664(9) 0.71848(18) 0.0450(12) Uani 1 1 d . . .
C19 C 0.5526(6) 0.27551(10) 0.6820(2) 0.0460(12) Uani 1 1 d . . .
C20 C 0.4838(6) 0.27678(10) 0.6218(2) 0.0649(15) Uani 1 1 d . . .
H20A H 0.4182 0.2592 0.6065 0.078 Uiso 1 1 calc R . .
C21 C 0.5116(7) 0.30386(12) 0.5844(2) 0.0650(14) Uani 1 1 d . . .
H21A H 0.4655 0.3047 0.5447 0.078 Uiso 1 1 calc R . .
C22 C 0.6092(7) 0.32912(11) 0.6088(3) 0.0614(14) Uani 1 1 d . . .
C23 C 0.6797(7) 0.32902(11) 0.6665(2) 0.0677(15) Uani 1 1 d . . .
H23A H 0.7440 0.3468 0.6816 0.081 Uiso 1 1 calc R . .
C24 C 0.6530(7) 0.30142(10) 0.7025(2) 0.0584(14) Uani 1 1 d . . .
H24A H 0.7049 0.3006 0.7414 0.070 Uiso 1 1 calc R . .


_geom_special_details            
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 O1 1.180(6) . ?
N1 O2 1.255(6) . ?
N1 C1 1.513(6) . ?
N2 O4 1.200(7) . ?
N2 O3 1.229(7) . ?
N2 C12 1.475(6) . ?
N3 O6 1.225(6) . ?
N3 O5 1.243(6) . ?
N3 C22 1.477(6) . ?
N4 C7 1.340(5) . ?
N4 C15 1.355(4) . ?
N5 C8 1.332(5) . ?
N5 C16 1.358(5) . ?
N6 C18 1.312(4) . ?
N6 C17 1.332(4) . ?
C1 C6 1.353(6) . ?
C1 C2 1.353(6) . ?
C2 C3 1.387(6) . ?
C2 H2A 0.9300 . ?
C3 C4 1.358(5) . ?
C3 H3A 0.9300 . ?
C4 C5 1.363(6) . ?
C4 C7 1.448(5) . ?
C5 C6 1.393(5) . ?
C5 H5A 0.9300 . ?
C6 H6A 0.9300 . ?
C7 C8 1.421(5) . ?
C8 C9 1.461(6) . ?
C9 C14 1.370(5) . ?
C9 C10 1.399(5) . ?
C10 C11 1.379(6) . ?
C10 H10A 0.9300 . ?
C11 C12 1.368(6) . ?
C11 H11A 0.9300 . ?
C12 C13 1.372(6) . ?
C13 C14 1.384(6) . ?
C13 H13A 0.9300 . ?
C14 H14A 0.9300 . ?
C15 C16 1.368(5) . ?
C15 C15 1.455(8) 3_656 ?
C16 C17 1.447(5) . ?
C17 C17 1.391(7) 3_656 ?
C18 C18 1.402(8) 3_656 ?
C18 C19 1.453(5) . ?
C19 C24 1.367(5) . ?
C19 C20 1.405(6) . ?
C20 C21 1.397(6) . ?
C20 H20A 0.9300 . ?
C21 C22 1.366(6) . ?
C21 H21A 0.9300 . ?
C22 C23 1.358(6) . ?
C23 C24 1.396(5) . ?
C23 H23A 0.9300 . ?
C24 H24A 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 N1 O2 125.9(6) . . ?
O1 N1 C1 117.1(6) . . ?
O2 N1 C1 117.0(6) . . ?
O4 N2 O3 123.2(6) . . ?
O4 N2 C12 119.6(7) . . ?
O3 N2 C12 117.2(7) . . ?
O6 N3 O5 124.2(5) . . ?
O6 N3 C22 117.1(6) . . ?
O5 N3 C22 118.5(6) . . ?
C7 N4 C15 118.9(3) . . ?
C8 N5 C16 119.5(4) . . ?
C18 N6 C17 119.8(3) . . ?
C6 C1 C2 124.6(5) . . ?
C6 C1 N1 117.0(6) . . ?
C2 C1 N1 118.4(6) . . ?
C1 C2 C3 116.6(5) . . ?
C1 C2 H2A 121.7 . . ?
C3 C2 H2A 121.7 . . ?
C4 C3 C2 122.0(5) . . ?
C4 C3 H3A 119.0 . . ?
C2 C3 H3A 119.0 . . ?
C5 C4 C3 118.5(4) . . ?
C5 C4 C7 120.1(4) . . ?
C3 C4 C7 121.4(5) . . ?
C4 C5 C6 121.8(4) . . ?
C4 C5 H5A 119.1 . . ?
C6 C5 H5A 119.1 . . ?
C1 C6 C5 116.4(5) . . ?
C1 C6 H6A 121.8 . . ?
C5 C6 H6A 121.8 . . ?
N4 C7 C8 119.1(4) . . ?
N4 C7 C4 114.8(4) . . ?
C8 C7 C4 126.0(4) . . ?
N5 C8 C7 120.1(4) . . ?
N5 C8 C9 114.6(4) . . ?
C7 C8 C9 125.3(4) . . ?
C14 C9 C10 119.5(4) . . ?
C14 C9 C8 120.9(4) . . ?
C10 C9 C8 119.5(4) . . ?
C11 C10 C9 120.7(5) . . ?
C11 C10 H10A 119.6 . . ?
C9 C10 H10A 119.6 . . ?
C12 C11 C10 118.1(5) . . ?
C12 C11 H11A 121.0 . . ?
C10 C11 H11A 121.0 . . ?
C13 C12 C11 122.3(5) . . ?
C13 C12 N2 117.6(6) . . ?
C11 C12 N2 120.1(6) . . ?
C12 C13 C14 119.2(5) . . ?
C12 C13 H13A 120.4 . . ?
C14 C13 H13A 120.4 . . ?
C9 C14 C13 120.0(5) . . ?
C9 C14 H14A 120.0 . . ?
C13 C14 H14A 120.0 . . ?
N4 C15 C16 121.4(4) . . ?
N4 C15 C15 119.5(2) . 3_656 ?
C16 C15 C15 119.0(2) . 3_656 ?
N5 C16 C15 119.4(4) . . ?
N5 C16 C17 118.6(4) . . ?
C15 C16 C17 122.0(4) . . ?
N6 C17 C17 119.9(2) . 3_656 ?
N6 C17 C16 121.3(4) . . ?
C17 C17 C16 118.8(2) 3_656 . ?
N6 C18 C18 120.0(2) . 3_656 ?
N6 C18 C19 115.2(4) . . ?
C18 C18 C19 124.8(2) 3_656 . ?
C24 C19 C20 117.7(4) . . ?
C24 C19 C18 123.4(4) . . ?
C20 C19 C18 118.9(4) . . ?
C21 C20 C19 121.6(4) . . ?
C21 C20 H20A 119.2 . . ?
C19 C20 H20A 119.2 . . ?
C22 C21 C20 117.2(5) . . ?
C22 C21 H21A 121.4 . . ?
C20 C21 H21A 121.4 . . ?
C23 C22 C21 123.5(5) . . ?
C23 C22 N3 120.5(5) . . ?
C21 C22 N3 115.9(6) . . ?
C22 C23 C24 118.1(5) . . ?
C22 C23 H23A 120.9 . . ?
C24 C23 H23A 120.9 . . ?
C19 C24 C23 121.8(5) . . ?
C19 C24 H24A 119.1 . . ?
C23 C24 H24A 119.1 . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.243
_refine_diff_density_min         -0.242
_refine_diff_density_rms         0.054
